Allen did not achieve his extraordinary success easily. Shortly after graduating from Western Michigan University with a degree in TV production, he was arrested for attempting to sell $43,000 worth of cocaine to a narcotics officer in the Kalamazoo airport. He pled guilty and cooperated fully with the police; his testimony reportedly led to the arrest of 21 other individuals. Out on bail after spending 60 days in a county jail, Allen and some friends attended a comedy club, Detroit's Comedy Castle. On a dare, he got up and performed stand-up for the first time, thereby discovering his true calling. His career had to wait, however, as he was sentenced to eight years imprisonment. More than once, the neophyte comic's quick verbal wit saved him from extreme unpleasantness behind bars as he amused his would-be attackers. Such an experience would have permanently derailed many lives but Allen utilized it to further his education through reading and formulated some goals. He served 28 months before his release.

After leaving prison, Allen secured a day job at an ad agency while working the comedy circuit at night. The next year, he started his own production company, Boxing Cat Productions, to produce graphic arts, design and commercials. By 1988, Allen was appearing on cable comedy specials, headlining the first of his own, "Men Are Pigs,” on Showtime in 1990. He had also impressed a Disney talent scout. The studio offered him leads in pilots based on the popular films "Turner & Hooch" and "Dead Poets Society" but Allen held out for a show based on his stand-up persona. His early material had been sexual and scatological in nature but he struck pay dirt when he began lampooning the kind of men's movement thinking popularized by the best-seller "Iron John.” Allen's material was well showcased by his sitcom as he played a know-it-all handyman with his own TV show, "Tool Time,” who was actually an overreaching klutz at home. With cute kids and a bright and beautiful wife (well played by Patricia Richardson).

After an appearance in a little-seen comedy performance film, Allen made his screen acting debut in Disney's holiday-oriented "The Santa Clause" (1994), in which he helps out an ailing Saint Nicholas and becomes closer to an estranged son. The film proved a surprise blockbuster, grossing over $144 million domestically. That same year, he also authored a best-selling book, "Don't Stand Too Close to a Naked Man" (Hyperion, 1994), in which he humorously examined aspects of his life and career. Allen finished out 1994 with his TV series, book and film all reigning in the number one positions in their respective arenas. He returned to the screen the following year in another Disney family picture, "Toy Story" (1995). Here he worked opposite Tom Hanks as the voice of Buzz Lightyear, a toy astronaut, in what was touted as the first full-length computer animated film.

Allen reprised his role in 1999's "Toy Story 2" a record-breaking box office smash which was hailed as one of the year's best animated films. He also starred in "Galaxy Quest" (1999), the hilarious spoof about a "Star Trek" type cast who enter into a real outer space adventure with aliens who believe the actors are the spaceship captains they play on television. Allen took a brief hiatus before returning to the screen as the lead in Barry Sonnenfeld's ensemble comedy "Big Trouble" (based on the satiric novel by Pulitzer Prize-winning humorist Dave Barry)-but the film, which featured an explosive device on an airplane in the plot-had its initial release date close to Sept. 11, 2001; as a result, it was delayed for several months and ultimately never attracted a large audience. He also re-teamed with his "Home Improvement" and "The Santa Claus" director for the comedy "Joe Somebody" (2002), playing an average guy who is bullied and trains to become a force to be reckoned with.

After appearing as a hit man in the mistaken identity indie comedy "Who Is Cletis Tout?", Allen returned to familiar territory in a mainstream holiday season box office sensation, reprising the role of Scott Calvin for "The Santa Claus 2" (2002). In keeping with his reputation as Hollywood's reigning king of the holiday comedy, he joined Jamie Lee Curtis as empty nest parents whose plans for a non-Christmas holiday getaway are scuttled by a last minute visit from their daughter in the over-the-top "Christmas with the Kranks" (2004). He next starred in the remake of the 1959 Disney classic “The Shaggy Dog” (2006), playing a workaholic district attorney whose long hours lead to neglecting a family that years for his attention. But when he’s transformed into the family’s beloved Bearded Collie after being infected by a genetic-mutation serum, he wants nothing more than be a good father. While not as appreciated or revered as its predecessor, “The Shaggy Dog” nonetheless took a healthy bite of box office dollars.

Allen upped the goofball factor for his next family feature, “Zoom” (2006), playing Captain Zoom, the over-the-hill leader of a once-prime group of superheroes called upon to train a new generation in order to save the planet before it’s too late. After a brief voice role reviving Buzz Lightyear as a car in Pixar’s box office smash “Cars” (2006), Allen returned a third time to the holiday role that endeared him to millions of families for “The Santa Clause 3: The Escape Clause” (2006). This time, the reluctant Kris Kringle is expecting a baby Claus with wife Carol (Elizabeth Mitchell), while trying to thwart Jack Frost (Martin Short) from taking over the North Pole. Allen moved on to costar in “Wild Hogs” (2007), a big, dumb and hugely successful ensemble comedy about four men (Allen, John Travolta, Martin Lawrence and William H. Macy) going through respective mid-life crises who embark on a freewheeling, cross-country motorcycle trip to prove their manhood. Despite a bevy of bad reviews, many of which complained about the bizarre, almost obsessive need for the four leads to constantly prove their heterosexuality onscreen, “Wild Hogs” dominated the box office its opening weekend, taking in almost $40 million and making it the first bona fide hit of 2007.